We analyze thousands of real estate agents in Highwood and nationwide to find you proven local professionals, for free.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for June 2026. *
* Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.
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Information and statistics on the latest trends in the Highwood real estate market. *
Feb 1, 2026 - Apr 30, 2026
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month data ending on quarter boundaries when available.
Rolling three-month supply and activity totals for the selected period.
Rolling three-month supply and activity totals for the selected period.
Rolling three-month supply and activity totals for the selected period.
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Feb 2026 - Apr 2026).
Highwood currently leans toward sellers, with the market gauge signaling a seller’s market despite a relatively high months of supply. Listings are sitting at about 6.9 months of supply in the latest rolling three-month period, much higher than a year ago. Even so, homes are spending a median of just 12 days on the market, down sharply from last year.
This mix of fast-selling homes and ample inventory helps explain why the gauge still favors sellers. The share of properties selling above list price has climbed to about three-quarters of recent sales, and the average sale-to-list ratio has moved above 103 percent on a year-over-year basis, showing buyers are often paying over asking. At the same time, active listings and new listings have both increased compared with a year ago, so buyers have more choices than they did previously.
Prices in this rolling three-month view tell a nuanced story. The typical home value is down significantly from a year earlier, yet median list prices are up strongly year over year, suggesting sellers are testing higher price points while buyers look for value. Sales volume has slipped compared with last year, even as pending sales have risen sharply, indicating more deals are in the pipeline. With these crosscurrents shaping negotiations for both sides, Agent Pronto can connect buyers and sellers with an experienced local agent who understands today’s Highwood market dynamics.
Highwood offers residents a welcoming, walkable community with vibrant local dining, shops, parks, and a friendly, active neighborhood vibe.
Highwood feels distinct from its North Shore neighbors by mixing a tight-knit, small city character with a lively restaurant and arts scene. Just north of Highland Park, it offers walkable blocks, local festivals, and renowned dining that draw both longtime residents and new arrivals.
Downtown Highwood centers on Green Bay Road, where you will find destination spots like Disotto Ristorante and Arriva Dolce alongside casual bars, music venues, and neighborhood services. Seasonal events, including evening markets and food festivals, give the area an energy that feels more urban than many nearby communities.
Outdoor access is a major part of life here. Residents enjoy the lakefront at Millard Park in nearby Lake Forest, local playgrounds, and athletic programs through the Park District of Highland Park. The Highwood Metra station offers a straightforward rail commute to Chicago, which adds appeal for professionals who want both city access and a strong community base.
Families appreciate access to North Shore School District 112 and Highland Park High School, and residents rely on nearby resources like the Highwood Public Library & Community Center for programs and services.
Whether you plan to buy or sell in Highwood, timing and preparation matter in this competitive pocket of the North Shore. Agent Pronto can connect you with a local real estate professional who understands the nuances of this market and can guide you confidently through your next move.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“Steve was always available, knowledgeable, and willing to listen to our thoughts and concerns about selling our home. More importantly, the selling of our home in tandem of purchasing a new home at the same time, went really well. If we needed to move again (heaven forbid) I wouldn't hesitate to have Steve again.”
“Working with Emir is always a pleasure. He was very helpful in coordinating work on our house for sale, working with vendors and providing valuable feedback on neccesary work vs. potential work items unlikely to generate return. We closed sale of house 3 weeks from time of first listing. I'd worked with Emir before and hope to do so again in the future.”
“Our house could be considered high end property in the neighborhood. Cinny worked hard to get it under the contract in a week and sold our house a little over a month. We are happy about the result. During the process, there were ups and downs which made us nervious. Cinny listened to our concerns and gave us professional advice.”
“Would use Lizette again, very easy to work with & very professional. Would recommend here 100% to Friends.”
“Renee O'Brien was very understanding, helpful, and kind .... knowledgable in the house situation and problem solving to move the sale along swiftly...”
““Working with Meldina Dervisevic to sell our single-family home in Wheeling was an excellent experience from start to finish. Her market knowledge, pricing strategy, and attention to detail helped us attract the right buyer quickly and confidently. Meldina guided us through every step of the process, communicated clearly, and handled negotiations with professionalism and care. Thanks to her expertise, our home sold smoothly and with great results. We highly recommend Meldina to anyone looking to sell their home.””
“Juan helped us immensely in buying our first home and answered every question we had. Would 100% recommend.”
“I had an amazing experience working with Erick when purchasing my new home. From the very beginning, he took the time to understand exactly what I was looking for and offered valuable insights into the housing market. Erick was incredibly knowledgeable, patient, and responsive, answering all my questions and guiding me through every step of the process. The process of finding the perfect home can be overwhelming, but Erick made it seamless. He was always available to schedule viewings at my convenience, and when we found the right place, he worked tirelessly to ensure my offer was competitive and that all the paperwork was handled efficiently. Thanks to Erick, I now own a home that I absolutely love. I highly recommend him to anyone looking for a dedicated and professional real estate agent.”
“I found a great agent! We were able to sell the property within three days after it was listed. It was a pleasure working with Diana Matichyn and her team. I would highly recommend her.”
“Larry is by far the most AMAZING Realtor. He was always very responsive to my calls, texts, request, etc. We built up such a great relationship through this crazy process, that even after we closed on our new home, he reached out to check on us. He is always looking to get the best deal for his clients. He is like family now to us and will always have his own seat next to the firepit in our backyard. I would DEFINETLY recommend Larry to anyone and everyone looking to buy or sell. AMAZING.. Can't say enough Great things about Larry.”
“Easily one of the best realtors, he was extremely friendly didn’t rush us for houses tours. He also showed my family and me plenty of houses on the market for months.”
There are more than 2 million real estate agents across the U.S., and you want to be sure the one you partner with is an experienced and trustworthy professional with strong local expertise covering the housing market in and around Highwood. Working with a proven agent will help you sell your home faster and for more money, and help you find your dream home at the best possible price.
Choosing a real estate agent to help you buy or sell property is one of the most important decisions you’ll make in your lifetime. You want to make sure your agent is an expert in your area, has a proven record helping people buy and sell similar homes to yours, and is well regarded by their previous clients. Let us know a few details about the property you are selling or the kind of home you want to buy, and Agent Pronto will match you with trusted real estate agents that have the experience you need. And before you interview an agent, check out our top five questions to ask a buyer’s agent and listing agent.
We consider performance metrics, close rates, specialties, and client reviews to qualify the best full-time agents. We then take the information you provide about the home you are selling or the kind of home you want to buy, and analyze the top local agents with the right experience for your specific needs. For more than a decade, we've helped hundreds of thousands of home buyers and sellers find the right agent. Get started now and find the perfect real estate agent.
No. Agent Pronto is a free service for home buyers and sellers and you are under no obligation to work with our recommended agents. Find your Highwood Realtor® or real estate agent today.
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